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J Chromatogr A. 2014 Aug 15;1355:206-10. doi: 10.1016/j.chroma.2014.06.017. Epub 2014 Jun 10.

Fluorescence derivatization method for sensitive chromatographic determination of zidovudine based on the Huisgen reaction.

Author information

  • 1Graduate School of Biomedical Sciences, Course of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
  • 2Graduate School of Biomedical Sciences, Course of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan. Electronic address: n-kuro@nagasaki-u.ac.jp.

Abstract

A novel pre-column fluorescence derivatization method for chromatographic analysis of azide compounds was developed based on the Huisgen reaction, which is a specific cycloaddition reaction between an alkyne and an azide. We designed and synthesized a fluorescent alkyne, 2-(4-ethynylphenyl)-4,5-diphenyl-1H-imidazole (DIB-ET) as a reagent. DIB-ET has a lophine skeleton carrying an alkyne acting as fluorophore and reactive center, respectively. In order to evaluate the practicality of DIB-ET, a high-performance liquid chromatography with fluorescence detection method was developed for the determination of zidovudine as a model of azide compound. Zidovudine could be reacted with DIB-ET in the presence of copper(II) sulfate and L-ascorbic acid as catalysts, and the formed derivative was detected fluorometrically. The proposed method allows sensitive and selective determination of zidovudine in plasma samples with the detection limit of 0.28ngmL(-1) at a S/N=3. Finally, the proposed method could be applied to determine the zidovudine concentration in rat plasma after administration of zidovudine without interference from biological components.

KEYWORDS:

Azide group; Fluorescence derivatization; Fluorescent alkyne; Huisgen reaction; Zidovudine

PMID:
25001338
DOI:
10.1016/j.chroma.2014.06.017
[PubMed - indexed for MEDLINE]
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